Phosphorus oxychloride → HCID 86588982, compound

HRID 1242792Notes

Reaction equation

HRID 1242792 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](O)[C:5]2[S:9][C:10]([CH2:12][CH3:13])=[CH:11][C:4]=2[N:3]=1.P(Cl)(Cl)([Cl:16])=O>>[CH3:1][C:2]1[N:7]=[C:6]([Cl:16])[C:5]2[S:9][C:10]([CH2:12][CH3:13])=[CH:11][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178435431HCID 178435431, compound

Product 1

HCID 86588982HCID 86588982, compoundYield 74%

Procedure

2-Methyl-4-hydroxy-6-ethylthienopyrimidine (0.71 g) was dissolved in phosphorus oxychloride (10 mL) and heated to reflux for 19 hours. After concentrating to dryness, the residue was diluted with water (20 mL) and the product was extracted with methylene chloride (3×5 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified on silica gel (50% ethyl acetate/hexane) giving 2-methyl-4-chloro-6-ethylthienopyrimidine (0.58 g). Yield=74%, Rf=0.73 (25% ethyl acetate/hexane).

Workup

  1. temperatureheated
  2. temperatureto reflux for 19 hours
  3. concentrationAfter concentrating to dryness
  4. additionthe residue was diluted with water (20 mL)
  5. extractionthe product was extracted with methylene chloride (3×5 mL)
  6. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-683309c9d95f437a89e00dc70e2e56e9
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

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